Sodium hydride → 2-(3,4-Dimethoxyphenyl)-4-(4-methylpiperazinylmethyl)thiazole

HRID 1699560Notes

Reaction equation

HRID 1699560 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:12][CH:13]=[C:14]([CH2:16]Cl)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[H-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:12][CH:13]=[C:14]([CH2:16][N:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]3)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 531671-MethylpiperazineHCID 20793964-(Chloromethyl)-2-(3,4-dimethoxyphenyl)-1,3-thiazole

Product 1

HCID 187072282-(3,4-Dimethoxyphenyl)-4-(4-methylpiperazinylmethyl)thiazoleYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of dimethylformamide were dissolved 860 mg of 2-(3,4-dimethoxyphenyl)-4-chloromethylthiazole and 320 mg of N-methylpiperazine. Thereto was added 130 mg of sodium hydride. The mixture was stirred at room temperature for 14 hours. The solvent was removed by distillation. The residue was extracted with chloroform. The extract was water-washed, dried and subjected to distillation to remove the solvent, The residue was dissolved in ethanol. To the solution was added ethanol saturated with hydrogen chloride gas, and the mixture was allowed to stand. The resulting crystals were collected by filtration washed with a small amount of ethanol, dried and recrystallized from ethanol to obtain 820 mg of 2-(3,4-dimethoxyphenyl)-4-(4-methylpiperazinylmethyl)thiazole.

Workup

  1. customThe solvent was removed by distillation
  2. extractionThe residue was extracted with chloroform
  3. washwashed
  4. customdried
  5. distillationsubjected to distillation
  6. customto remove the solvent
  7. dissolutionThe residue was dissolved in ethanol
  8. additionTo the solution was added ethanol saturated with hydrogen chloride gas
  9. filtrationThe resulting crystals were collected by filtration
  10. washwashed with a small amount of ethanol
  11. customdried
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8d4bca7445e344babff2309ed74f46e2
Source dataset
uspto-grants-2002_02
Patent number
USRE037556E1

Reaction notes

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